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From Proto-Italic*doleō(“hurt, cause pain”), from Proto-Indo-European*dolh₁éyeti(“divide”), from *delh₁-(“cut”). The sense development is thus assumed to be that "divide" came to mean "divide someone into pieces, hurt". Compare dolō(“hew, fashion, devise”).
doleo in Gaffiot, Félix (1934) Dictionnaire illustré latin-français, Hachette.
Carl Meißner, Henry William Auden (1894) Latin Phrase-Book, London: Macmillan and Co.
I am pained, vexed, sorry: doleo aliquid, aliqua re, de and ex aliqua re
I am sorry for you: tuam vicemdoleo
De Vaan, Michiel (2008) Etymological Dictionary of Latin and the other Italic Languages (Leiden Indo-European Etymological Dictionary Series; 7), Leiden, Boston: Brill, →ISBN, page 176